Photo by Meghan Watters

Windward Side vacation rentals

We found 13 vacation rentals — enter your dates for availability

your current months are March, 2024 and April, 2024.
March 2024
April 2024
Scroll through and select from vacation rentals in Windward Side to find one that's perfect for your trip. Whether you’re staying in a vacation home with friends, family, or just with your pet, you'll find the best amenities for hanging out with the people that matter most, which might include WiFi and a washer and dryer. Whatever you're looking for, you're sure to find a rental that has what everyone needs, including accessible or non-smoking choices.

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The lush setting of Windward Side is ready to explore

The jungle, ocean views and mountains are a perfect backdrop to your vacation home in Windward Side. This scenic city allures visitors with its hiking and diving. A vacation rental can help make your stay complete. Many rentals come with a full kitchen and laundry facilities.

Exploring the natural features in Windward Side

Whether you're an active traveler or just want to take in the scenery, Windward Side is a great place to get outside. Here are a few of the area's most enchanting sights, all within 30 miles (48.2 km) of the city center:

  • Cove Bay Beach (1.2 mi / 2 km)
  • Well's Bay Beach (1.6 mi / 2.6 km)
  • Mt Scenery (0.7 mi / 1.1 km)

How to get to and around Windward Side

The nearest airport is in Saba (SAB-Juancho E. Yrausquin), located 1.3 mi (2.1 km) from the city center. If you can't find a flight that works for your travel itinerary, you might consider flying into Oranjestad (EUX-F.D. Roosevelt), which is 19 mi (30.5 km) away.

Frequently asked questions

What is the most popular type of vacation rental accommodation in Windward Side?

The most sought-after types of vacation rentals in Windward Side are villas. After something a little different? Vrbo has many options to match our guests' unique requirements, so you'll see vacation homes in loads of shapes and sizes. The perfect home away from home is waiting for you — get yours today.

How much does it cost to rent a vacation rental in Windward Side?

The average price for a vacation rental in Windward Side is determined by several factors, such as season, property type and length of stay. Whether you're searching for a villa with space for extended family or a cozy cabin for just you and your sweetheart, just add your dates of travel to view stays that offer great value.

How much does it cost to rent a beach house in Windward Side?

When you travel and the size and style of the property will influence how much you'll pay for your beachside vacation rental. Type in your Windward Side travel dates to see your options on Vrbo. Can't live without a private pool? Use our filters to pick the amenities and features you need.

Are there pet-friendly vacation rentals in Windward Side?

Pack a squeezy toy and a bone for your pooch because Windward Side has six stays that throw out the welcome mat to pets. Let your happy hound join in with the family fun at one of our pet-friendly vacation rentals on Vrbo. Simply enter your travel dates then check our "Pets allowed" filter box.

Can I rent a house with a pool in Windward Side?

Add a whole new level of fun to your trip by staying in one of the three houses with a private pool in Windward Side. Use our handy search filter to find the kind of property you want on Vrbo, and then spend leisurely days splish-splashing around in a swimming pool that's all yours.

What are popular rental amenities in Windward Side?

When it comes to rental amenities that guests are looking for in Windward Side, an ocean view, a water view and a chef are the most popular. With Vrbo vacation homes, there are choices to fit your taste and style, whether you're going on a trip with friends, family or even pets.

Are there large group vacation rentals in Windward Side?

Take your pick of three Vrbo vacation homes in Windward Side that can accommodate a group of five or more people. You'll get all the privacy and room you need to kick back with your loved ones — and no one else.

Are there vacation rentals in Windward Side that welcome kids?

Windward Side has five family-friendly vacation homes to choose from. And finding a stay that welcomes youngsters is a breeze with Vrbo's "Properties good for families" filter. On top of having the whole place to yourselves, you'll have access to perks and amenities like multiple bedrooms, full kitchens and private pools.

What are the top attractions for families in Windward Side?

There are loads of wonderful things to see and do with the family in Windward Side, such as:

  • Cove Bay Beach
  • Wells Bay Beach
  • Dutch Museum of Saba

Can I find two-bedroom vacation rentals in Windward Side?

Gather your nearest and dearest and enjoy a relaxing escape in one of the two two-bedroom vacation rentals Windward Side has to offer.

Are there vacation rentals with WiFi in Windward Side?

Windward Side has two vacation rentals with WiFi, so you'll be able to stay connected when you're away. Simply check the "WiFi" box in our handy search filter to find the perfect property. From streaming TV shows with the family to scrolling social media, these Vrbo homes make it a cinch to go online.

How can I find vacation rentals with air conditioning in Windward Side?

Windward Side has three vacation rentals where you'll be able to relax and recharge in air-conditioned comfort. To find a property on Vrbo that offers this perk, enter your travel dates and use the handy filters to select the "air conditioning" box.

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